I think all three can be worn through all seasons. The grey is more cool imo. The tan is perfect;not too orange. It really depends on your wardrobe and your preference of a neutral. I used to own the grey St. Louis. It was my first but I eventually got tired of it. I used to dislike the black/tan, but now that’s my favorite color (aside from goyard’s green color). The grey is more subdued than the black/tan and the black/black looks the most chic imo. I would get the one you’re drawn to most when you see them in person. Personally, I wouldn’t get the black tan in the mini Anjou…the contrast tan piping to the black canvas looks a bit odd on such a small bag imo, but this is just a personal preference thing as well. Good luck in deciding! No matter which color you pick, I’m sure you’ll get a lot of use out of this adorable mini bag!